Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
Bartleby Related Questions Icon

Related questions

Question

how do i do this ?

expand button
expand button
Expert Solution
Check Mark
Step 1 Introduction

On hydrolysis, esters undergo cleavage to produce carboxylic acid and alcohol. The reaction occurs in the presence of an aqueous acid(H2SO4) or an aqueous base(NaOH).

The mechanism of base hydrolysis involves the following steps.

  1. The nucleophilic attack of carbonyl carbon by Hydroxyl ion(OH-) resulting in tetrahedral intermediate.
  2. The tetrahedral intermediate disintegrates by the release of the alkoxide group reforming carbonyl group.
  3. Thus, acid is produced from the tetrahedral intermediate, and the alkoxide group converts to alcohol.

The mechanism of acid hydrolysis involves the following steps.

  1. Protonation of ester carbonyl making it more electrophilic.
  2. Water oxygen acts as the nucleophile attacking the electrophilic C=O group forming a tetrahedral intermediate.
  3. Deprotonation of water group attached to the tetrahedral intermediate.
  4. Alkoxide group is made a good leaving group by protonation.
  5. Neutral methanol gets released. 
  6. Deprotonation of oxonium ion results in a carboxylic acid.

NOTE: According to Bartleby guidelines, one question should be answered. I am answering Q5.

Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY